In Praise of Polly, Sugar, and the Advice Column As Personal Essay

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In the fall of 2011, I was a mess. A combination of calamity and poor decision-making, coupled with several sea changes in my life, left me feeling raw and skinned. It was one of those times where song lyrics suddenly have intensely personal meaning, when the impossibility of seeing your future feels like the cruelest feature of human existence. I lost friends and alienated people, drank too much, took everything too seriously. I earnestly recited portions of The Crack-Up. I visited a voodoo psychic that lived under my apartment. It would have been an excellent time to recruit me into a cult.

During that time I found myself feverishly, compulsively asking people for advice. I polled strangers about the ways they lived, the ways they coped with things, whether I would be OK in the end. And when my friends’ patience had worn out and I had been gently and not-so-gently rebuffed at parties enough times, I turned to advice columns. For something like three months, I consumed them all, obsessively: Savage Love, Dear Prudence, the Dear Abby and Ann Landers archives, all of the assorted Ask A ______ columns on the Awl.

Part of it was the hope that I would hit upon The Answer, that magical formula of how to live your life that will make all your conflicts resolve, your skin clear up, your cellulite disappear, and your enemies wither. Part of it was taking in the vast spectrum of other people’s problems, that process of acknowledging your own human messiness and hoping that there is, in the world, a corresponding messiness that someone has worked through. Because even though situations that these advice columnists responded to varied wildly, at the center there was always the same question: How can I make it OK?

It was at that time that I happily stumbled upon The Rumpus’ Dear Sugar, an advice column originally written by Steve Almond and then passed on to the novelist and memoirist Cheryl Strayed. Much praise has been heaped on Strayed’s work already. If her name is familiar to you, it’s likely that her writing voice is as well. In an age where snark and sarcasm is currency, Strayed’s column was strong and sincere. Her authority didn’t come from expertise or education, but from the depth of living and coping and handling and working through.

Most advice columnists, in order to stay sane and keep their jobs, necessarily separate themselves from the people they answer. This is especially the case when you’re writing about relationships, or your audience begins to suspect that you are simply trying things in order to have fodder for the column. (The Carrie Bradshaw trap is one that many young women fell into during the early aughts.) The trick is to avoid writing about yourself whenever possible, to keep the focus on the person asking the question. But Strayed approached the column less as the traditional question-answer format, and more as a forum for rich personal essays. She wove in anecdotes from her own life in the way that people naturally do when consulted by a friend. She made the limitations and benefits of her own experience explicit in a way that amplified her authority, cemented the trust you had in her as a reader. When one reader sent her in a half-joking cynical lament about the WTF? of the world, Strayed responded with a tale of her own sexual abuse at the hands of her paternal grandfather. “Ask better questions, sweet pea. The fuck is your life,” she wrote. “Answer it.” When another reader asked her about advice she would have given her 20-something self, Strayed’s reply was both pragmatic, beautiful, and heartbreaking:

Most things will be okay eventually, but not everything will be. Sometimes you’ll put up a good fight and lose. Sometimes you’ll hold on really hard and realize there is no choice but to let go. Acceptance is a small, quiet room.

One hot afternoon during the era in which you’ve gotten yourself ridiculously tangled up with heroin you will be riding the bus and thinking what a worthless piece of crap you are when a little girl will get on the bus holding the strings of two purple balloons. She’ll offer you one of the balloons, but you won’t take it because you believe you no longer have a right to such tiny beautiful things. You’re wrong. You do.

The collection of Dear Sugar columns, Tiny, Beautiful Things, is named after this column. It’s the kind of book that people will press into your hands fervently, eyes gleaming, page pre-dogeared for consultation. It’s the kind of book people buy even though the majority of its contents are on the internet, just to have it readily accessible at all times. I have a copy on my iPhone, and a couple in reserve in my apartment to dole out to friends going through hard times.

Strayed stopped writing the column in 2012, shortly after the release of her memoir Wild. Into the fray of the advice column as personal essay stepped Heather Havrilesky, who began penning an “existential advice column” for the Awl in 2012 under the name Polly Esther. Havrilesky’s column, which appeared on the Awl until last week when she announced that she was moving operations to The Cut, had a different approach than Strayed’s. Her voice is more biting, her style a little looser and less meditated, her advice less like a sage post-punk aunt and more like a cool, slightly manic older sister. She writes about her marriage and children, about her mistakes and fears, about interacting with men in bars and cursing loudly and stumbling through life the way that we all do, but still keeping your heart open enough to savor the things that are good. In one particularly inspired column, she advises a woman on how to find love by touching on the much-hyped feud between Jimmy Kimmel and Kanye West:

So here’s where we land: You need to tell tepid to fuck right off, Kanye-style. If you vow right now that the second you see tepid, you’re going to back up and say “No fucking thanks,” and move on without looking back, then your self-esteem will immediately bounce back from years of abuse. That means retiring the soliloquy about how great you are. That means no more badgering… Because tepid is everywhere. Tepid is the air we breathe. Listen to me: We can’t do anything right. We can’t say what we mean, we can’t be ourselves, we can’t age, we can’t talk about feelings, we can’t fuck up. This is how it feels to be a woman, motherfucker. The world is filled with human beings who want us to shut up and shake our asses, point blank, the end. Can you fucking imagine if we had our own Kanye?

Havrilesky and Strayed’s styles and audiences are different, but both women hit upon an aspect of what Dan Savage jokingly refers to as the “advice industrial complex” that’s not usually explored in syndicated columns.  It’s that not everyone asking for advice actually wants solutions.

This is what I realized after reading Sugar, after following Polly every Wednesday, after paging through queries about distant spouses and block party etiquette and anxious wedding planning, after picking the pieces of myself back up and returning to a saner emotional place, moving apartments, taking a new job, mending some of the relationships I had destroyed and leaping back into the long, hard work of trying to be a decent person. It’s that when people unspool their tale of woe and ask for your advice, a large part what they’re hoping is simply to be heard. It’s that when I was looking for advice, what I really wanted was acknowledgement. It’s that the thing that you want to hear during the hardest points in your life is not always that things will be OK, which they mostly turn out to be. What you need to hear is yes, life is hard and strange for everyone. That your pain is valid. That you are seen. That the messiness of humanity is a feature, not a flaw. That we are all improvising here.

What I needed was the kind of nourishment that Polly and Sugar offered, the aching truth that there are no easy fixes, but there are people who will listen. What I needed to hear is that we are all in this together, that grief and complication and wonder and triumph are things everyone experiences. The secret of advice columns is that no one has the answers. We can only offer each other the solutions that we create for ourselves, the Rube Goldberg emotional mechanisms and justifications we create to move forward. We can only keep going and keep hoping.

Follow Margaret Eby on Twitter @margareteby

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